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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Villas in Pienza and around

Villa with pool and garden
Outdoor dining

Villa with pool and garden

10.0 out of 10, Exceptional, (1)
"Top"
Villa with pool and garden
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (82)
"Luigi was very helpful. We had a chef 3 nights that he helped facilitate. Beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!
Il Poggio dell'Eremita
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (53)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
The price is €156
includes taxes & fees
12 Sept - 13 Sept
Il Poggio dell'Eremita
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Exterior

Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool

10.0 out of 10, Exceptional, (54)
"We had the trip of a lifetime at this wonderful home. Sherri, the property manager, made sure we had everything we needed upon arrival and organized a truffle hunt and wine tasting with her lovely local connections. She also introduced us to her favorite restaurants nearby (they were amazing) and told us where to shop. And the house itself is stunning- it should be in a movie about Tuscany. Cannot wait to go back!"
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Terrace/patio

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

10.0 out of 10, Exceptional, (52)
"we had a amazing time staying at this beautiful Villla. I highly recommend it to anyone!"
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Villa with private pool, air conditioning near wineries at 3km from village
Outdoor dining

Villa with private pool, air conditioning near wineries at 3km from village

9.4 out of 10, Exceptional, (42)
"Guido’s home in Tuscany is great! My family had an awesome time enjoying the pool, the near by wineries and a cooking class at the villa. The house is rustic, charming and in a great location. The beds are a bit old and the showers were a little small but overall the house fit all the needs of my family. The pool was also excellent and the views from the pool area are incredible. Whenever we needed anything it was always answered quickly. Thanks for an awesome stay!"
Villa with private pool, air conditioning near wineries at 3km from village
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Outdoor dining

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany

10.0 out of 10, Exceptional, (42)
"We spent a few nice days in spring '25 in Cortona"
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
ancient villa with pool and park in total privacy
Exterior

ancient villa with pool and park in total privacy

9.8 out of 10, Exceptional, (26)
"Nice place for a relaxing vacation. Perfect hub for trips to towns like Arezzo, Peruggia or Siena."
ancient villa with pool and park in total privacy
Wonderful private villa for 4 guests with A/C, pool, WIFI, TV, terrace and parking
Exterior

Wonderful private villa for 4 guests with A/C, pool, WIFI, TV, terrace and parking

9.8 out of 10, Exceptional, (29)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
Wonderful private villa for 4 guests with A/C, pool, WIFI, TV, terrace and parking
Luxury Cortona view hilltop Villa
Outdoor pool, a heated pool

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (48)
"The location and accommodations are perfect for a family. Nestled in the Italian countryside providing easy access to the nearby renaissance villages, art and landscapes and the people of Italy. The accommodations that Mieke has provided will only put a smile on your face."
Luxury Cortona view hilltop Villa
Villa with swimming pool and large garden, nestled in the hills of Maremma
Terrace/patio

Villa with swimming pool and large garden, nestled in the hills of Maremma

Villa with swimming pool and large garden, nestled in the hills of Maremma
Villa Podere Belvedere
Pool

Villa Podere Belvedere

9.8 out of 10, Exceptional, (14)
"Thank you for making our trip so enjoyable - great hospitality!"
Villa Podere Belvedere
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Property grounds

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

9.2 out of 10, Wonderful, (45)
"We liked our stay very much"
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Exterior

Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

9.8 out of 10, Exceptional, (98)
"🌟 A Perfect Stay in a Beautiful Villa 🌟 We had a wonderful time staying at this villa! It was incredibly spacious and comfortably accommodated all six of us. The house was thoughtfully equipped with everything we could possibly need, making it feel like a true home away from home. The shared pool—only between three villas—was clean, peaceful, and felt very private, which was a lovely bonus. One of our favorite parts of the stay was exploring the scenic walking trails through the surrounding...
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
XIII Century Tower with Private Panoramic Pool
Exterior

XIII Century Tower with Private Panoramic Pool

XIII Century Tower with Private Panoramic Pool
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Exterior

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

10.0 out of 10, Exceptional, (2)
"Beautiful villa in fantastic location . Easy to get to many places and attractions. Well equipped and very comfy beds. Lovely helpful owner. Would love to return."
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Villa Larniano, With Private Pool And View On Vineyard
Outdoor dining

Villa Larniano, With Private Pool And View On Vineyard

10.0 out of 10, Exceptional, (65)
"We had a lovely stay with 7 of us. There was plenty of area to walk and explore. We loved our wine tour with Lorenzo and our dinner with chef Robin. The house is close to the big grocery store and Siena."
Villa Larniano, With Private Pool And View On Vineyard
I Cipressi, 5 bedrooms with pool near Cortona
Exterior

I Cipressi, 5 bedrooms with pool near Cortona

10.0 out of 10, Exceptional, (2)
"The home is beautiful: Wonderfully decorated and lovingly cared for. Views are amazing; Caretakers are lovely and we all fell in love with Zorro the Dog. My only complaint is that the beds were only box springs and could have been more comfortable."
I Cipressi, 5 bedrooms with pool near Cortona
Tuscany Villa with Breathtaking View at Dotholiday
Exterior

Tuscany Villa with Breathtaking View at Dotholiday

9.8 out of 10, Exceptional, (16)
"Absolutely delight to stay in the house on top of the Tuscany world. Great pool and fabulous support from Manuela on restaurants. Will definitely go back in the future!"
Tuscany Villa with Breathtaking View at Dotholiday
Le Colombelline 12, Emma Villas
Exterior

Le Colombelline 12, Emma Villas

Le Colombelline 12, Emma Villas
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pienza Hotel Reviews

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

10/10 Excellent
"Just need better parking "
Maricela 1-night trip
Posted 3 days ago
Hotel Relais II Chiostro di Pienza

Frequently asked questions

How much do villas in Pienza cost?
Rates for villas in Pienza range between €156 and €156 per night. Whatever your budget, you're sure to find a place that fits the bill with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Pienza?
Pack your suitcase and pick from 1604 villas in Pienza. For a family escape, a getaway with pals or anything in between, Expedia will help you find the right place in just a click or two.
Why book your villa in Pienza with Expedia?
With Expedia, it's easy to find your dream villa in Pienza. Holidaying with the kids? Use our helpful filters to search for stays with amenities like WiFi and a pool. If you have a certain budget, select how much you'd like to spend and your preferred star rating. We'll help you find the right stay in tune with your taste and style.